Remarkable enhancement in the DNA-binding ability of C2-fluoro substituted pyrrolo[2,1-c][1,4]benzodiazepines and their anticancer potential

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 4, 2009, Pages 1557-1572

  Kamal, Ahmed ^a   Rajender, ^a   Reddy, D Rajasekhar ^a   Reddy, M Kashi ^a   Balakishan, G ^a   Shaik, T Basha ^a   Chourasia, Mukesh ^a   Sastry, G Narahari ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Anticancer activity; DNA binding affinity; Fluoro; Piperazine; Pyrrolobenzodiazepine

Indexed keywords

1,10 [(PROPANE 1,3 DIYL)DIOXY]BIS(7 METHOXY 2,2 DIFLUORO 1,2,3,11A TETRAHYDRO 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE); 1,10 [[1,4 DI(PROPANE 1,3 DIYL)HEXAHYDROPIPERAZINE]DIOXY]BIS(2 FLUORO 7 METHOXY 1,2,3,11A TETRAHYDRO 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE); DSB 120; PYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE; SJG 136; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DNA DENATURATION; DRUG DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; RESTRICTION MAPPING; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; BENZODIAZEPINES; CELL LINE, TUMOR; DNA; DNA RESTRICTION ENZYMES; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; PYRROLIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 60049086079     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.12.068     Document Type: Article

References (42)

1. Sawyers C. Nature 432 (2004) 294
2. Li Q., and Xu W. Curr. Med. Chem. Anticancer Agents 5 (2005) 53
3. Cozzi P., Mongelli N., and Suarato A. Curr. Med. Chem. Anticancer Agents 4 (2004) 93
4. Marais J.S.C., and Onderstepoort. J. Vet. Sci. Anim. Ind. 18 (1943) 203
5. Fried J., and Sabo E.F. J . Am . Chem . Soc . 76 (1954) 1455
6. Hertel L.W., Kroin J.W., and Tustin J.M. J. Org. Chem. 53 (1988) 2406
7. Hertel L.W., Boder G.B., Kroin J.S., Rinzel S.M., Poore G.A., Todd G.C., and Grindey G.B. Cancer Res. 50 (1990) 4417
8. Cozzi P., Mongelli N., and Suarato A. Curr. Med. Chem. AnticancerAgents 4 (2004) 93
9. Wu Y.-J., Davis C.D., Dworetzky S., Fitzpatrick W.C., Harden D., He H., Knox R.J., Newton A.E., Philip T., Polson C., Sivarao D.V., Sun L.-Q., Tertyshnikova S., Weaver D., Yeola S., Zoeckler M., and Sinz M.W. J. Med. Chem. 46 (2003) 3778
10. O'Neil I.A., Thompson S., Kalindjian S.B., and Jenkins T.C. Tetrahedron Lett. 44 (2003) 7809
11. Rajski S.R., and Williams R.M. Chem. Rev. 98 (1998) 2723
12. Kamal A., Laxman N., Ramesh G., Neelima K., and Kondapi A.K. Chem. Commun. (2001) 437
13. Thurston D.E. In: Neidle S., and Waring M.J. (Eds). Molecular Aspects of Anticancer Drug-DNA Interactions Vol. 1 (1993), The Macmillan Press Ltd, London, UK p 54
14. Yang X.-L., and Wang A.H.-J. Phramacol . Ther. 83 (1999) 181
15. Morris S.J., Thurston D.E., and Nevell T.G. J. Antibiot. 43 (1990) 1286
16. Marris, S. M. Design, Synthesis and Evaluation of a Sequence Selective DNA-Cleaving Agents Based on the Pyrrolo[2,1- c][1,4]benzodiazepine Ring System: Investigating of the DNA-Reactive Species Ph.D. Thesis University of Portsmouth, Portsmouth, UK; 1992.
17. Bose D.S., Thompson A.S., Ching J., Hartely J.A., Berardini M.D., Jenkins T.C., Neidle S., Hurley L.H., and Thurston D.E. J. Am. Chem. Soc. 114 (1992) 4939
18. Gregson S.J., Howrd P.W., Jenkins T.C., Kelland L.R., and Thurston D.E. Chem. Commun. (1999) 797
19. Kamal A., Ramesh G., Laxman N., Ramulu P., Srinivas O., Neelima K., Kondapi A.K., Srinu V.B., and Nagarajaram H.A. J. Med. Chem. 45 (2002) 4679
20. Kamal A., Ramesh G., Srinivas O., Ramulu P., Laxman N., Rehana T., Deepak M., Achary M.S., and Nagarajaram H.A. Bioorg. Med. Chem. 12 (2004) 5427
21. Tuker J.A., Allwine D.A., Grega K.C., Barbachyn M.R., Klock J.L., and Adamski J.L. J. Med. Chem. 41 (1998) 3727
22. Bruno A.M., Asis S.E., and Gaozza C.H. Pharmazie 56 (2001) 361
23. Najajreh Y., Perez J.M., Navarro-Ranninger C., and Gibson D. J. Med. Chem. 45 (2002) 5189
24. Kamal A., Reddy P.S.M.M., and Reddy D.R. Bioorg. Med. Chem. Lett. 14 (2004) 2669
25. Kamal A., Reddy P.S.M.M., Reddy D.R., Laxman E., and Murthy Y.L.N. Bioorg. Med. Chem. Lett. 14 (2004) 5699
26. Kamal A., Reddy D.R., and Reddy P.S.M.M. Bioorg. Med. Chem. Lett. 17 (2007) 803
27. Qiu X., and Qing F. J. Org. Chem. 67 (2002) 7162
28. Dc Luca L., Giacomelli G., and Porcheddu A. Org. Lett. 3 (2001) 3041
29. Demange L., Menez A., and Dugave C. Tetrahedron Lett. 39 (1998) 1169
30. Thurston D.E., Murty V.S., Langley D.R., and Jones G.B. Synthesis (1990) 81
31. Kamal, A.; Reddy, D. R.; Rajendar. U.S. Patent Appl. No. 11/715592; Indian Patent Appl. No. 0669DEL2006.
32. Kamal A., Reddy P.S.M.M., and Reddy D.R. Tetrahedron Lett. 44 (2003) 2857
33. Kamal, A.; Rajender.; Reddy, M. K.; Balakishan, G. Indian Patent Appl. No. 0669DEL2006.
34. Thurston D.E., Bose D.S., Thompson A.S., Howard P.W., Leoni A., Croker S.J., Jenkins T.C., Neidle S., Hartley J.A., and Hurley L.H. J. Org. Chem. 61 (1996) 8141
35. Collier D.A., Thuong N.T., and Helene C. J. Am. Chem. Soc. 113 (1991) 1457
36. Sumner W., and Bennett G.N. Nucleic Acids Res. 9 (1981) 2105
37. Puvvada M.S., Hartley J.A., Jenkins T.C., and Thurston D.E. Nucleic Acids Res. 21 (1993) 3671
38. Kamal A., Naseer A.K., Reddy K.S., Kaleem S.A., Kumar S.M., Aarti J., Subrata S., and Surekha Z. Bioorg. Med. Chem. Lett. 17 (2007) 5345
39. Kamal A., Kumar P.P., Seshadri B.N., Srinivas O., Kumar S.M., Subratha S., Nisha K., Aarti S.J., and Surekha M.Z. Bioorg. Med. Chem. 16 (2008) 3895
40. Gregson S.J., Howard P.W., Gullick D.R., Hamaguchi A., Corcoran K.E., Brooks N.A., Hartley J.A., Jenkins T.C., Patel S., Guille M.J., and Thurston D.E. J. Mem. Chem. 47 (2004) 1161
41. Jones G.B., Davey C.L., Jenkins T.C., Kamal A., Kneale G.G., Neidle S., Webster G.D., and Thurston D.E. Anti-cancer Drug Des. 5 (1990) 249
42. Connaughie A.W.M., and Jenkins T.C. J. Med. Chem. 38 (1995) 3488